CA2622701A1 - Derives d'amino-aza-adamantane et procedes d'utilisation - Google Patents
Derives d'amino-aza-adamantane et procedes d'utilisation Download PDFInfo
- Publication number
- CA2622701A1 CA2622701A1 CA002622701A CA2622701A CA2622701A1 CA 2622701 A1 CA2622701 A1 CA 2622701A1 CA 002622701 A CA002622701 A CA 002622701A CA 2622701 A CA2622701 A CA 2622701A CA 2622701 A1 CA2622701 A1 CA 2622701A1
- Authority
- CA
- Canada
- Prior art keywords
- dec
- azatricyclo
- group
- carboxylic acid
- amide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title claims abstract description 136
- MWLWPDIWTONGOU-UHFFFAOYSA-N 1-azatricyclo[3.3.1.13,7]decan-2-amine Chemical class C1C(C2)CC3CC1C(N)N2C3 MWLWPDIWTONGOU-UHFFFAOYSA-N 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 181
- 102000019315 Nicotinic acetylcholine receptors Human genes 0.000 claims abstract description 43
- 108050006807 Nicotinic acetylcholine receptors Proteins 0.000 claims abstract description 43
- 230000027455 binding Effects 0.000 claims abstract description 15
- -1 2,3-dihydro-1H-indolyl Chemical group 0.000 claims description 289
- 125000000217 alkyl group Chemical group 0.000 claims description 100
- 229910052739 hydrogen Inorganic materials 0.000 claims description 98
- 229910052757 nitrogen Inorganic materials 0.000 claims description 83
- 125000003118 aryl group Chemical group 0.000 claims description 67
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 53
- 239000001257 hydrogen Substances 0.000 claims description 50
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 44
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 43
- 125000003545 alkoxy group Chemical group 0.000 claims description 42
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 42
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 39
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 38
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 34
- 125000001188 haloalkyl group Chemical group 0.000 claims description 34
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 34
- 125000004414 alkyl thio group Chemical group 0.000 claims description 33
- 125000003342 alkenyl group Chemical group 0.000 claims description 32
- 229910052736 halogen Inorganic materials 0.000 claims description 32
- 150000002367 halogens Chemical group 0.000 claims description 32
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 31
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 31
- 230000000694 effects Effects 0.000 claims description 31
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 31
- 208000035475 disorder Diseases 0.000 claims description 30
- 125000001424 substituent group Chemical group 0.000 claims description 30
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 29
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 29
- 125000000623 heterocyclic group Chemical group 0.000 claims description 28
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 27
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 27
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 27
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 26
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 26
- 125000001072 heteroaryl group Chemical group 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 22
- 208000024827 Alzheimer disease Diseases 0.000 claims description 18
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 17
- 229910052717 sulfur Inorganic materials 0.000 claims description 16
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
- 206010012289 Dementia Diseases 0.000 claims description 14
- 201000000980 schizophrenia Diseases 0.000 claims description 13
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- 239000000651 prodrug Substances 0.000 claims description 11
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- PTNWHEHDBNNKEO-UHFFFAOYSA-N 5-thiophen-2-ylthiophene-2-carboxylic acid Chemical compound S1C(C(=O)O)=CC=C1C1=CC=CS1 PTNWHEHDBNNKEO-UHFFFAOYSA-N 0.000 claims description 10
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 10
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 10
- 125000004429 atom Chemical group 0.000 claims description 10
- 208000010877 cognitive disease Diseases 0.000 claims description 10
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 10
- RIIAHEIBOHZBED-UHFFFAOYSA-N thieno[2,3-c]pyridine-5-carboxylic acid Chemical compound C1=NC(C(=O)O)=CC2=C1SC=C2 RIIAHEIBOHZBED-UHFFFAOYSA-N 0.000 claims description 10
- GHTDODSYDCPOCW-UHFFFAOYSA-N 1h-indole-6-carboxylic acid Chemical compound OC(=O)C1=CC=C2C=CNC2=C1 GHTDODSYDCPOCW-UHFFFAOYSA-N 0.000 claims description 9
- DMPZJACLHDWUFS-UHFFFAOYSA-N 1,3-benzothiazole-6-carboxylic acid Chemical compound OC(=O)C1=CC=C2N=CSC2=C1 DMPZJACLHDWUFS-UHFFFAOYSA-N 0.000 claims description 8
- DRBLTQNCQJXSNU-UHFFFAOYSA-N 1-benzothiophene-3-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CSC2=C1 DRBLTQNCQJXSNU-UHFFFAOYSA-N 0.000 claims description 8
- GZHWABCBKGMLIE-UHFFFAOYSA-N 2-methyl-3h-benzimidazole-5-carboxylic acid Chemical compound C1=C(C(O)=O)C=C2NC(C)=NC2=C1 GZHWABCBKGMLIE-UHFFFAOYSA-N 0.000 claims description 8
- ADRFTNFHVKVATK-UHFFFAOYSA-N 5-[3-(trifluoromethyl)phenyl]furan-2-carboxylic acid Chemical compound O1C(C(=O)O)=CC=C1C1=CC=CC(C(F)(F)F)=C1 ADRFTNFHVKVATK-UHFFFAOYSA-N 0.000 claims description 8
- QZLSBOVWPHXCLT-UHFFFAOYSA-N 5-chlorothiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=C(Cl)S1 QZLSBOVWPHXCLT-UHFFFAOYSA-N 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 206010061218 Inflammation Diseases 0.000 claims description 8
- 201000010099 disease Diseases 0.000 claims description 8
- 230000006870 function Effects 0.000 claims description 8
- IENZCGNHSIMFJE-UHFFFAOYSA-N indole-5-carboxylic acid Chemical compound OC(=O)C1=CC=C2NC=CC2=C1 IENZCGNHSIMFJE-UHFFFAOYSA-N 0.000 claims description 8
- 230000004054 inflammatory process Effects 0.000 claims description 8
- 125000001624 naphthyl group Chemical group 0.000 claims description 8
- 125000001544 thienyl group Chemical group 0.000 claims description 8
- QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 claims description 8
- 230000029663 wound healing Effects 0.000 claims description 8
- DYSJMQABFPKAQM-UHFFFAOYSA-N 1-benzothiophene-2-carboxylic acid Chemical compound C1=CC=C2SC(C(=O)O)=CC2=C1 DYSJMQABFPKAQM-UHFFFAOYSA-N 0.000 claims description 7
- UOBYKYZJUGYBDK-UHFFFAOYSA-N 2-naphthoic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CC=C21 UOBYKYZJUGYBDK-UHFFFAOYSA-N 0.000 claims description 7
- XUFDYUSOQQYQRL-UHFFFAOYSA-N 5-(2-nitrophenyl)-2-furoic acid Chemical compound O1C(C(=O)O)=CC=C1C1=CC=CC=C1[N+]([O-])=O XUFDYUSOQQYQRL-UHFFFAOYSA-N 0.000 claims description 7
- QGMFBCDNJUZQBZ-UHFFFAOYSA-N 5-phenylthiophene-2-carboxylic acid Chemical compound S1C(C(=O)O)=CC=C1C1=CC=CC=C1 QGMFBCDNJUZQBZ-UHFFFAOYSA-N 0.000 claims description 7
- HQULGJDHOPDURG-UHFFFAOYSA-N 5-pyridin-2-ylthiophene-2-carboxylic acid Chemical compound S1C(C(=O)O)=CC=C1C1=CC=CC=N1 HQULGJDHOPDURG-UHFFFAOYSA-N 0.000 claims description 7
- 210000004204 blood vessel Anatomy 0.000 claims description 7
- 210000003169 central nervous system Anatomy 0.000 claims description 7
- 230000012010 growth Effects 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- FVZJIAUYFDQQKJ-DQEYMECFSA-N n-[4-[(4as,10br)-8,9-dimethoxy-2-methyl-3,4,4a,10b-tetrahydro-1h-benzo[c][1,6]naphthyridin-6-yl]phenyl]-4-methylbenzenesulfonamide Chemical compound N([C@H]1CCN(C)C[C@H]1C=1C=C(C(=CC=11)OC)OC)=C1C(C=C1)=CC=C1NS(=O)(=O)C1=CC=C(C)C=C1 FVZJIAUYFDQQKJ-DQEYMECFSA-N 0.000 claims description 7
- 230000004770 neurodegeneration Effects 0.000 claims description 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 6
- OFFSPAZVIVZPHU-UHFFFAOYSA-N 1-benzofuran-2-carboxylic acid Chemical compound C1=CC=C2OC(C(=O)O)=CC2=C1 OFFSPAZVIVZPHU-UHFFFAOYSA-N 0.000 claims description 6
- SNBYTKLWZRHESA-UHFFFAOYSA-N 1-benzothiophene-5-carboxylic acid Chemical compound OC(=O)C1=CC=C2SC=CC2=C1 SNBYTKLWZRHESA-UHFFFAOYSA-N 0.000 claims description 6
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 claims description 6
- JWZQJTGQFHIRFQ-UHFFFAOYSA-N 2,3-dihydro-1,4-benzodioxine-6-carboxylic acid Chemical compound O1CCOC2=CC(C(=O)O)=CC=C21 JWZQJTGQFHIRFQ-UHFFFAOYSA-N 0.000 claims description 6
- 239000005711 Benzoic acid Substances 0.000 claims description 6
- 239000003693 atypical antipsychotic agent Substances 0.000 claims description 6
- 229940127236 atypical antipsychotics Drugs 0.000 claims description 6
- 235000010233 benzoic acid Nutrition 0.000 claims description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 6
- KMAKOBLIOCQGJP-UHFFFAOYSA-N indole-3-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CNC2=C1 KMAKOBLIOCQGJP-UHFFFAOYSA-N 0.000 claims description 6
- 208000027061 mild cognitive impairment Diseases 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- 125000000335 thiazolyl group Chemical group 0.000 claims description 6
- BHXVYTQDWMQVBI-UHFFFAOYSA-N 1h-indazole-3-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=NNC2=C1 BHXVYTQDWMQVBI-UHFFFAOYSA-N 0.000 claims description 5
- IFLKEBSJTZGCJG-UHFFFAOYSA-N 3-methylthiophene-2-carboxylic acid Chemical compound CC=1C=CSC=1C(O)=O IFLKEBSJTZGCJG-UHFFFAOYSA-N 0.000 claims description 5
- 208000030507 AIDS Diseases 0.000 claims description 5
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 5
- 201000010374 Down Syndrome Diseases 0.000 claims description 5
- 201000011240 Frontotemporal dementia Diseases 0.000 claims description 5
- 208000000609 Pick Disease of the Brain Diseases 0.000 claims description 5
- 206010039966 Senile dementia Diseases 0.000 claims description 5
- 206010044688 Trisomy 21 Diseases 0.000 claims description 5
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 5
- 230000007278 cognition impairment Effects 0.000 claims description 5
- 230000006735 deficit Effects 0.000 claims description 5
- 125000002541 furyl group Chemical group 0.000 claims description 5
- 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims description 5
- 210000004558 lewy body Anatomy 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- VDVJGIYXDVPQLP-UHFFFAOYSA-N piperonylic acid Chemical compound OC(=O)C1=CC=C2OCOC2=C1 VDVJGIYXDVPQLP-UHFFFAOYSA-N 0.000 claims description 5
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 5
- NDMFETHQFUOIQX-UHFFFAOYSA-N 1-(3-chloropropyl)imidazolidin-2-one Chemical compound ClCCCN1CCNC1=O NDMFETHQFUOIQX-UHFFFAOYSA-N 0.000 claims description 4
- SJJCQDRGABAVBB-UHFFFAOYSA-N 1-hydroxy-2-naphthoic acid Chemical compound C1=CC=CC2=C(O)C(C(=O)O)=CC=C21 SJJCQDRGABAVBB-UHFFFAOYSA-N 0.000 claims description 4
- KGKZHHIUOZGUNP-UHFFFAOYSA-N 1h-indazole-4-carboxylic acid Chemical compound OC(=O)C1=CC=CC2=C1C=NN2 KGKZHHIUOZGUNP-UHFFFAOYSA-N 0.000 claims description 4
- YHMXJZVGBCACMT-UHFFFAOYSA-N 2,1,3-benzothiadiazole-5-carboxylic acid Chemical compound C1=C(C(=O)O)C=CC2=NSN=C21 YHMXJZVGBCACMT-UHFFFAOYSA-N 0.000 claims description 4
- MSRFFOJBAXRZJL-UHFFFAOYSA-N 2-pyridin-4-yl-3h-1,3-thiazole-2-carboxylic acid Chemical compound C=1C=NC=CC=1C1(C(=O)O)NC=CS1 MSRFFOJBAXRZJL-UHFFFAOYSA-N 0.000 claims description 4
- FGKCNTGJZXHKFJ-UHFFFAOYSA-N 2-thiophen-2-yl-1,3-thiazole-4-carboxylic acid Chemical compound OC(=O)C1=CSC(C=2SC=CC=2)=N1 FGKCNTGJZXHKFJ-UHFFFAOYSA-N 0.000 claims description 4
- AEDWMWQOFJYAGN-UHFFFAOYSA-N 5-(2-methyl-1,3-thiazol-4-yl)thiophene-2-carboxylic acid Chemical compound S1C(C)=NC(C=2SC(=CC=2)C(O)=O)=C1 AEDWMWQOFJYAGN-UHFFFAOYSA-N 0.000 claims description 4
- JETRXAHRPACNMA-UHFFFAOYSA-N 5-chloro-1-benzofuran-2-carboxylic acid Chemical compound ClC1=CC=C2OC(C(=O)O)=CC2=C1 JETRXAHRPACNMA-UHFFFAOYSA-N 0.000 claims description 4
- DUDBNCNNJMOLCC-UHFFFAOYSA-N 5-thiophen-2-yl-1h-pyrazole-3-carboxylic acid Chemical compound N1N=C(C(=O)O)C=C1C1=CC=CS1 DUDBNCNNJMOLCC-UHFFFAOYSA-N 0.000 claims description 4
- ZRCGKWSNRRTAJY-UHFFFAOYSA-N 6-chloro-2h-chromene-3-carboxylic acid Chemical compound ClC1=CC=C2OCC(C(=O)O)=CC2=C1 ZRCGKWSNRRTAJY-UHFFFAOYSA-N 0.000 claims description 4
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- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
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- JXHSGSLIUHNKRC-UHFFFAOYSA-N thieno[2,3-b]thiophene-5-carboxylic acid Chemical compound C1=CSC2=C1C=C(C(=O)O)S2 JXHSGSLIUHNKRC-UHFFFAOYSA-N 0.000 claims description 4
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- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 3
- OUIALVLMUYKKKS-UHFFFAOYSA-N 1,2,3-benzothiadiazole-5-carboxylic acid Chemical compound OC(=O)C1=CC=C2SN=NC2=C1 OUIALVLMUYKKKS-UHFFFAOYSA-N 0.000 claims description 3
- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 claims description 3
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims description 3
- ZEAKWWWXCZMODH-UHFFFAOYSA-N 2-amino-1,3-benzothiazole-6-carboxylic acid Chemical compound C1=C(C(O)=O)C=C2SC(N)=NC2=C1 ZEAKWWWXCZMODH-UHFFFAOYSA-N 0.000 claims description 3
- UXGVMFHEKMGWMA-UHFFFAOYSA-N 2-benzofuran Chemical compound C1=CC=CC2=COC=C21 UXGVMFHEKMGWMA-UHFFFAOYSA-N 0.000 claims description 3
- VNHBYKHXBCYPBJ-UHFFFAOYSA-N 5-ethynylimidazo[1,2-a]pyridine Chemical compound C#CC1=CC=CC2=NC=CN12 VNHBYKHXBCYPBJ-UHFFFAOYSA-N 0.000 claims description 3
- VCNGNQLPFHVODE-UHFFFAOYSA-N 5-methylthiophene-2-carboxylic acid Chemical compound CC1=CC=C(C(O)=O)S1 VCNGNQLPFHVODE-UHFFFAOYSA-N 0.000 claims description 3
- BFPLMTPHDFFMTG-UHFFFAOYSA-N [1,3]oxazolo[5,4-b]pyridine Chemical compound C1=CN=C2OC=NC2=C1 BFPLMTPHDFFMTG-UHFFFAOYSA-N 0.000 claims description 3
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 3
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims description 3
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
- 125000004230 chromenyl group Chemical group O1C(C=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 3
- YRTCKZIKGWZNCU-UHFFFAOYSA-N furo[3,2-b]pyridine Chemical compound C1=CC=C2OC=CC2=N1 YRTCKZIKGWZNCU-UHFFFAOYSA-N 0.000 claims description 3
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- ZNRWXIJAFJJYPI-UHFFFAOYSA-N 6-chloroimidazo[1,2-a]pyridine-8-carboxylic acid Chemical compound OC(=O)C1=CC(Cl)=CN2C=CN=C12 ZNRWXIJAFJJYPI-UHFFFAOYSA-N 0.000 claims description 2
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- 239000011734 sodium Substances 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
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- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- UXAWXZDXVOYLII-YUMQZZPRSA-N tert-butyl (1s,4s)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate Chemical compound C1[C@@H]2N(C(=O)OC(C)(C)C)C[C@H]1NC2 UXAWXZDXVOYLII-YUMQZZPRSA-N 0.000 description 1
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
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- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/04—Drugs for genital or sexual disorders; Contraceptives for inducing labour or abortion; Uterotonics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
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- A—HUMAN NECESSITIES
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- A61P25/00—Drugs for disorders of the nervous system
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- A—HUMAN NECESSITIES
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- A61P9/00—Drugs for disorders of the cardiovascular system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Reproductive Health (AREA)
- Pain & Pain Management (AREA)
- Heart & Thoracic Surgery (AREA)
- Gynecology & Obstetrics (AREA)
- Cardiology (AREA)
- Psychiatry (AREA)
- Endocrinology (AREA)
- Pregnancy & Childbirth (AREA)
- Rheumatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Psychology (AREA)
- Hospice & Palliative Care (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US72032605P | 2005-09-23 | 2005-09-23 | |
| US60/720,326 | 2005-09-23 | ||
| US11/517,064 US7897766B2 (en) | 2005-09-23 | 2006-09-07 | Amino-aza-adamantane derivatives and methods of use |
| US11/517,064 | 2006-09-07 | ||
| PCT/US2006/036360 WO2007038058A2 (fr) | 2005-09-23 | 2006-09-19 | Derives d'amino-aza-adamantane et procedes d'utilisation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2622701A1 true CA2622701A1 (fr) | 2007-04-05 |
Family
ID=37894920
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002622701A Abandoned CA2622701A1 (fr) | 2005-09-23 | 2006-09-19 | Derives d'amino-aza-adamantane et procedes d'utilisation |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US7897766B2 (fr) |
| EP (2) | EP2476681A3 (fr) |
| JP (1) | JP5031752B2 (fr) |
| CN (1) | CN102816165A (fr) |
| CA (1) | CA2622701A1 (fr) |
| WO (1) | WO2007038058A2 (fr) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8314119B2 (en) * | 2006-11-06 | 2012-11-20 | Abbvie Inc. | Azaadamantane derivatives and methods of use |
| US8076350B2 (en) | 2006-12-22 | 2011-12-13 | Abbott Laboratories | Spirocyclic azaadamantane derivatives and methods of use |
| US8168791B2 (en) | 2007-03-23 | 2012-05-01 | Abbott Laboratories | Aminomethyl azaadamantane derivatives and methods of use thereof |
| US8163914B2 (en) * | 2007-03-23 | 2012-04-24 | Abbott Laboratories | Acetamide and carboxamide derivatives of azaadamantane and methods of use thereof |
| EP2139891B1 (fr) * | 2007-03-23 | 2012-09-05 | Abbott Laboratories | Dérivés 4-substitués d'azaadamantane et leurs procédés d'utilisation |
| US20090123945A1 (en) | 2007-06-27 | 2009-05-14 | Abbott Laboratories | Cholinergic/serotoninergic receptor and uses thereof |
| EP2231657A1 (fr) * | 2007-11-21 | 2010-09-29 | Abbott Laboratories | Dérivés d'alcane azabicyclique à substitution biaryle en tant que modulateurs de l'activité du récepteur nicotinique de l'acétylcholine |
| JP5544550B2 (ja) * | 2008-08-01 | 2014-07-09 | 国立大学法人 千葉大学 | ポジトロン断層撮影法および該方法に用いるポジトロン放出化合物 |
| KR20130108586A (ko) | 2010-09-23 | 2013-10-04 | 애브비 인코포레이티드 | 아자아다만탄 유도체의 일수화물 |
| EP3233087B1 (fr) | 2014-12-16 | 2019-10-02 | Axovant Sciences GmbH | Composés amide de quinuclidine à substituants géminal, en tant qu'agonistes des récepteurs nicotiniques de l'acétylcholine 7 |
| AU2016274694A1 (en) | 2015-06-10 | 2018-01-18 | Axovant Sciences Gmbh | Aminobenzisoxazole compounds as agonists of A7-nicotinic acetylcholine receptors |
| JP2018523707A (ja) | 2015-08-12 | 2018-08-23 | アクソバント サイエンシズ ゲーエムベーハー | α７−ニコチン性アセチルコリン受容体のアゴニストとしてのジェミナル置換アミノベンゾイソオキサゾール化合物 |
| EP3409659B1 (fr) * | 2016-01-26 | 2020-12-30 | Tohoku University | Dérivé d'adamantane et son utilisation |
| MY198328A (en) | 2017-08-02 | 2023-08-24 | Neusignal Therapeutics Inc | Adamantylmethylamine Derivative and use Thereof as Pharmaceutical |
| CA3220039A1 (fr) | 2021-06-14 | 2022-12-22 | Jr. David St. Jean | Derives d'uree pouvant etre utilises pour traiter le cancer |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| FR543954A (fr) * | 1921-11-25 | 1922-09-12 | Application du flexible à la transmission du cultivateur au semoir | |
| FR2543954B1 (fr) | 1983-04-08 | 1985-09-06 | Nativelle Sa Ets | Acylamino-4 aza-1 adamantanes, procede pour leur preparation et application en therapeutique |
| GB8523211D0 (en) | 1985-09-19 | 1985-10-23 | Beecham Group Plc | Compounds |
| FR2629363B1 (fr) * | 1988-03-29 | 1991-10-11 | Rubinstein Inc H | Particules d'emulsion gelifiees et leur utilisation, notamment en cosmetologie |
| EP0350130A3 (fr) * | 1988-07-07 | 1991-07-10 | Duphar International Research B.V | 1H-indazoles 1,7-annelés substitués |
| US5260303A (en) | 1991-03-07 | 1993-11-09 | G. D. Searle & Co. | Imidazopyridines as serotonergic 5-HT3 antagonists |
| US5280028A (en) | 1992-06-24 | 1994-01-18 | G. D. Searle & Co. | Benzimidazole compounds |
| US5434151A (en) | 1992-08-24 | 1995-07-18 | Cytomed, Inc. | Compounds and methods for the treatment of disorders mediated by platelet activating factor or products of 5-lipoxygenase |
| US5840903A (en) * | 1992-07-27 | 1998-11-24 | G. D. Searle & Co. | 4-aminomethyl-1-azaadamantane derived benzamides |
| US5334151A (en) * | 1993-03-03 | 1994-08-02 | Santilli Albert N | Device for capping and uncapping a hypodermic needle |
| JP3235913B2 (ja) | 1993-07-30 | 2001-12-04 | エーザイ株式会社 | アミノ安息香酸誘導体 |
| US5399562A (en) * | 1994-02-04 | 1995-03-21 | G. D. Searle & Co. | Indolones useful as serotonergic agents |
| US6111111A (en) | 1997-10-23 | 2000-08-29 | Kuraray Co., Ltd. | Intermediates for producing pyridine derivatives |
| US5952339A (en) | 1998-04-02 | 1999-09-14 | Bencherif; Merouane | Pharmaceutical compositions and methods of using nicotinic antagonists for treating a condition or disorder characterized by alteration in normal neurotransmitter release |
| US6057446A (en) * | 1998-04-02 | 2000-05-02 | Crooks; Peter Anthony | Certain 1-aza-tricyclo [3.3.1-13,7 ] decane compounds |
| US5986100A (en) * | 1998-04-02 | 1999-11-16 | Crooks; Peter Anthony | Pharmaceutical compositions and methods for use |
| ES2199561T3 (es) | 1998-04-02 | 2004-02-16 | Targacept, Inc. | Derivados de azatriciclo(3.3.1.1)decano y composiciones farmaceuticas que los contienen. |
| US6093724A (en) | 1998-08-18 | 2000-07-25 | Ucb, S.A. | Muscarinic agonists and antagonists |
| BR0011534A (pt) | 1999-05-24 | 2002-02-26 | Targacept Inc | Alquilaminas aril substituìdas capazes de ativação de receptores colinérgicos nicotìnicos |
| US20010031771A1 (en) * | 1999-05-24 | 2001-10-18 | Gary Maurice Dull | Pharmaceutical compositions and methods for use |
| AU2001265831B9 (en) * | 2000-07-04 | 2006-08-31 | Neurosearch A/S | Aryl and heteroaryl diazabicycloalkanes, their preparation and use |
| DE10121215A1 (de) * | 2001-04-30 | 2002-10-31 | Merck Patent Gmbh | Dihydro-imidazo[4,5-e]indol- und 7H-Pyrrolo[3,2-f]chinoxalin Derivate als nikotinische Acetylcholinrezeptor Liganden und/oder serotonerge Liganden |
| US7300933B2 (en) | 2002-05-07 | 2007-11-27 | Neurosearch A/S | Diazabicyclic biaryl derivatives |
| US20050065178A1 (en) | 2003-09-19 | 2005-03-24 | Anwer Basha | Substituted diazabicycloakane derivatives |
| US7399765B2 (en) | 2003-09-19 | 2008-07-15 | Abbott Laboratories | Substituted diazabicycloalkane derivatives |
-
2006
- 2006-09-07 US US11/517,064 patent/US7897766B2/en not_active Expired - Fee Related
- 2006-09-19 CA CA002622701A patent/CA2622701A1/fr not_active Abandoned
- 2006-09-19 EP EP12151398A patent/EP2476681A3/fr not_active Withdrawn
- 2006-09-19 CN CN2012102652392A patent/CN102816165A/zh active Pending
- 2006-09-19 WO PCT/US2006/036360 patent/WO2007038058A2/fr active Application Filing
- 2006-09-19 EP EP06803813A patent/EP1926731A2/fr not_active Withdrawn
- 2006-09-19 JP JP2008532311A patent/JP5031752B2/ja not_active Expired - Fee Related
-
2011
- 2011-01-24 US US13/012,130 patent/US8586746B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| EP2476681A3 (fr) | 2012-10-03 |
| WO2007038058A3 (fr) | 2007-07-05 |
| US20080234308A2 (en) | 2008-09-25 |
| JP2009508956A (ja) | 2009-03-05 |
| US7897766B2 (en) | 2011-03-01 |
| WO2007038058A2 (fr) | 2007-04-05 |
| US8586746B2 (en) | 2013-11-19 |
| US20110118301A1 (en) | 2011-05-19 |
| JP5031752B2 (ja) | 2012-09-26 |
| CN102816165A (zh) | 2012-12-12 |
| EP2476681A2 (fr) | 2012-07-18 |
| US20070072892A1 (en) | 2007-03-29 |
| EP1926731A2 (fr) | 2008-06-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |
Effective date: 20140320 |